Investigation of photophysical properties of 1,8-naphthalimides with an extended conjugation on naphthalene moiety via Suzuki coupling reaction

Eunju Jang, Ting Ding, Meng Xie, Haishi Cao

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Five 4-substituted 1,8-naphthalimides (1-5), with an extended conjugation on the naphthalene ring, have been synthesized via Suzuki coupling reaction. These derivatives showed a large Stokes shift (up to 200 nm) and longer emission due to the increase of conjugation. Besides strong solvation effect, the low quantum yield were observed in protic solvents compared to in aprotic solvents. The anion forms of 1-5 obtained from reacting with NaH gave a significant red-shift for both absorption and emission spectra. These results provided a new strategy for preparation of fluorescent dyes with a long emission on the basis of 1,8-naphthalimde structure by using Suzuki coupling reaction.

Original languageEnglish (US)
Pages (from-to)145-150
Number of pages6
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume364
DOIs
StatePublished - Sep 1 2018

Fingerprint

Naphthalimides
Naphthalene
conjugation
naphthalene
Solvation
Quantum yield
Fluorescent Dyes
red shift
Anions
solvation
emission spectra
Negative ions
Dyes
dyes
anions
Derivatives
absorption spectra
preparation
rings
shift

Keywords

  • 1,8-Naphthalimide
  • Photophysical properties
  • Suzuki coupling reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Cite this

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title = "Investigation of photophysical properties of 1,8-naphthalimides with an extended conjugation on naphthalene moiety via Suzuki coupling reaction",
abstract = "Five 4-substituted 1,8-naphthalimides (1-5), with an extended conjugation on the naphthalene ring, have been synthesized via Suzuki coupling reaction. These derivatives showed a large Stokes shift (up to 200 nm) and longer emission due to the increase of conjugation. Besides strong solvation effect, the low quantum yield were observed in protic solvents compared to in aprotic solvents. The anion forms of 1-5 obtained from reacting with NaH gave a significant red-shift for both absorption and emission spectra. These results provided a new strategy for preparation of fluorescent dyes with a long emission on the basis of 1,8-naphthalimde structure by using Suzuki coupling reaction.",
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T1 - Investigation of photophysical properties of 1,8-naphthalimides with an extended conjugation on naphthalene moiety via Suzuki coupling reaction

AU - Jang, Eunju

AU - Ding, Ting

AU - Xie, Meng

AU - Cao, Haishi

PY - 2018/9/1

Y1 - 2018/9/1

N2 - Five 4-substituted 1,8-naphthalimides (1-5), with an extended conjugation on the naphthalene ring, have been synthesized via Suzuki coupling reaction. These derivatives showed a large Stokes shift (up to 200 nm) and longer emission due to the increase of conjugation. Besides strong solvation effect, the low quantum yield were observed in protic solvents compared to in aprotic solvents. The anion forms of 1-5 obtained from reacting with NaH gave a significant red-shift for both absorption and emission spectra. These results provided a new strategy for preparation of fluorescent dyes with a long emission on the basis of 1,8-naphthalimde structure by using Suzuki coupling reaction.

AB - Five 4-substituted 1,8-naphthalimides (1-5), with an extended conjugation on the naphthalene ring, have been synthesized via Suzuki coupling reaction. These derivatives showed a large Stokes shift (up to 200 nm) and longer emission due to the increase of conjugation. Besides strong solvation effect, the low quantum yield were observed in protic solvents compared to in aprotic solvents. The anion forms of 1-5 obtained from reacting with NaH gave a significant red-shift for both absorption and emission spectra. These results provided a new strategy for preparation of fluorescent dyes with a long emission on the basis of 1,8-naphthalimde structure by using Suzuki coupling reaction.

KW - 1,8-Naphthalimide

KW - Photophysical properties

KW - Suzuki coupling reaction

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